Cadillac Jac

"Mitch dates a widow."

Font Size

Mitchell Bellamy smiled that dreamy smile of his.

“Do you want to watch me masturbate?”

His eyes were honest blue in a tanned and leathery face. At seventy years old, he had little time for game playing. His dinner date with sixty-three-year-old Julie Johnson, farm widow, wasn’t going well; their conversation had difficulty connecting in any meaningful way. It was unlikely they would have sex, but perhaps she might give him an old-fashioned. So Mitch chose a straightforward approach to getting his penis out of his pants as they sat in his top-down blue Cadillac convertible, with white leather seats, in Julie’s farmyard, on a warm August night.

The garish pole light lit up the face of her home and three outbuildings. Mitch and Julie and the white leather seats stood in stark relief to the deep black of the night.

Grey-haired, frock-wearing, and matronly stout, Julie was genuinely surprised by Mitch’s question. Dinner had been awkward for both of them. Julie’s late husband used to buy his farming needs from Mitch’s Farm Emporium, plus they all went to the same Scandinavian Lutheran church. So Mitch and Julie knew each other, but they weren’t friends. So far, a date with Mitch had been a bad idea, but here he was, ready to pull out his penis and stroke it in front of her. Maybe he was more interesting than their dinner had proven him to be.

“If you show me yours, Mitch, I’ll show you mine.” Julie’s eyes twinkled. Was Mitch all talk, or was there more to him? Her hopes were up.

Mitch’s eyes widened, and a smile slowly came over his face. Maybe tonight wasn’t going to be a complete loss.  Unzipping and unhooking his trousers, Mitch pulled his lightly swollen member through the access hole of his white BVDs. He let his member, a short, slender sausage, relax on his leg under the yard light.

“I’m a grower, not a shower,” Mitch explained.

“I live on a farm, Mitch. I know how those things work.”

“Do you want to touch it?”

“No, Mitch, I don’t. I would like to see how big it gets, though. Show me what you got, and if you want to masturbate, I’ll watch. Been a while since I’ve seen a man’s dick.”

Mitch placed his hand on his member to encourage it to lengthen. His penis became chubby and then firm, and finally, it filled out to a comely length.

Julie smiled pleasantly; Mitch’s equipment still worked! So many men can get it up but not keep it up at his age. Medication takes the man out of so many men.

“That’s a nice dick, Mitch. Nice size and nice shape. Did your wife like it?”

Mitch tugged his erection.

“Yes, before she took sick, of course. We were intimate until that happened.”

“Do you masturbate a lot now?”

Mitch paused. With a touch of pride in his voice, Mitch replied.

“Two, maybe three, times a week as the moods strike.”

“That’s good, Mitch. Orgasms are good for you. Well, I guess it’s my turn now.”

Julie slid her mid-length country dress up her thighs, lifted her butt, and shimmied her scarlet lace panties until they slipped off over the only pair of decent heels she owned. She stretched her panties across the white dashboard, then she found the electric seat buttons and laid the seat back until there was enough room for her to put her heels on the dash. Opening her legs, Julie knew she was making a special memory for Mitch. Her late husband used to say, “Make me a memory to remember, Honey.” This memory was going to be a good one for Mitch.

Seeing Julie’s freshly-shaved cleft under the pole light, Mitch licked his lips and thought, Oh, God! This is happening! Widow Johnson is showing me her pussy, and she shaved it for me!

Pressing his seat button, Mitch reclined until his body was elongated, and his cock stood straight up. He lifted his ass and tugged his pants to his knees; Mitch slid his hardened cock and grey-haired balls out of the white BVDs.

Julie could see his foreskin retreat and reveal his ‘shroom, full and taut and engorged.

“It’s a manly cock, Mitch. It suits you.”

“It’d be nice if you stroked me,” Mitch smiled that dreamy smile of his.

“Ah, but you offered to masturbate for me. I want to keep everything else for another time, assuming there is one,” Julie teased.

Mitch chuckled softly. She was interested in him after all.

He switched his cock to his left hand and snaked his right towards Julie’s pussy. Stroking his cock in front of Widow Johnson and touching her pussy hit all the right fantasy buttons. The wife of another man! Ok, the man was dead, but still, this qualified as sex with another man’s wife!

Julie opened her legs a little more and relaxed into Mitch’s masturbation. It had been a long time since another man had his fingers on her. She was wet, and she let his fingers do as they pleased.

“You have a nice touch, Mitch. Don’t stop doin’ what you’re doing.”

With her head back and looking away from the pole light, she could see the sky was full of stars. She and her late husband had many nights of hot sex under the stars but never in a Cadillac convertible. White leather seats were more comfortable than the horse blanket they used, and yet orgasms are good for the soul no matter how you get them or who gives them to you.

Julie turned her head to watch Mitch stroke his cock. He was taking long, unhurried strokes up and down the length of it. He had not yet reached the point of hurrying his release along. On Julie, his fingers were talented, or maybe more experienced than talented, but they woke sleeping memories of earlier times with her late husband.

Julie moaned and complimented Mitch. “That’s nice, Mitch. You can touch my pussy like this any time. Go ahead and make me happy to be with you, Mitch.”

Mitch was practically in heaven! It had been years since he masturbated with a woman. Plus, she was complimenting him! Mitch stroked faster.

Julie picked up on his cue that it was time for him to release.

“Honey, it’s ok to release now. I want to see it. Are you going to cum on these seats? No, wait for just a second!”

Julie took her feet off the dash and quickly shifted positions to sit on the door and spread her legs toward him.

“Look at my pussy, Mitch. It’s ready for your hot seed. You have some for me, don’t you, Honey? Here, cum on my panties instead of your seat!”

Julie flicked her panties off the dash towards his cock. Mitch caught them in his right hand and, without missing a stroke, buried his cockhead into Widow Johnson’s scarlet red silk panties. He grunted as he ejaculated, and he jerked hard several times. As he clutched her panties to his seventy-year-old cock, he thoroughly soaked them with semen.

Mitch breathed heavily from the exertion.

Julie smiled her approval.

“I guess you’ve been doing a lot of practicing.”

Mitch smiled that dreamy smile of his. “Whew, that was a good one.”

“Did everything make it into my panties?”

Mitch looked for signs of leakage and nodded his head.

“Uh, huh, it did.”

“Here, let me have them.”

Mitch removed them from around his shrinking member and handed them to Julie.

“Mmm, Mitch, you sure know how to fill a woman’s panties. I’ll give you that. Now, there’s just one more thing to do with these panties soaked with your jizz.”

Julie pressed the panties to her pussy and pushed them inside her cunt until a triangular pennant of scarlet-red lace poked out between her labia. It was the hottest thing Mitch had seen in the past forty years!

“I’m going to leave them in here for a while. Next time, I might let you ejaculate inside me, assuming you invite me out again, but for right now, your sperm in my panties and my panties in my pussy will do nicely.”

Julie pulled her dress down and carefully slid back into the seat before opening the car door. Mitch pulled up his white BVDs and his trousers and made himself presentable again.

Mitch turned towards Widow Johnson. He had that dreamy smile on his face again.

“We’re not going to kiss, Mitch. We’ll save that for another time if there is one. Thanks for dinner.”

And with that goodbye, Widow Johnson went into her house and straight to her bedroom for her vibrator, orgasm on the forefront of her mind.

Outside, Mitch backed down the driveway to the main road. He failed to notice a young couple from the Scandinavian Church sneaking out of Widow Johnson’s barn. They had been watching the action in the Cadillac the entire time. If Mitch had seen the couple, he wouldn’t wonder in the future who gave him the nickname “Cadillac Jack.”

Published 3 years ago

Leave a Comment